Propylene Glycol → 1-(Tosyloxy)-2-propanol

HRID 1252666Notes

Reaction equation

HRID 1252666 reaction equation
[CH2:1]([OH:5])[CH:2]([OH:4])[CH3:3].N1C=CC=CC=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>C(Cl)Cl>[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([O:5][CH2:1][CH:2]([OH:4])[CH3:3])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1030Propylene GlycolHCID 1049PyridineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 109988101-(Tosyloxy)-2-propanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 200 ml of methylene chloride were dissolved 38 g of 1,2-propanediol and 44 g of pyridine and, then, 95 g of p-toluenesulfonyl chloride was added gradually over a period of 15 minutes. The reaction was further conducted at room temperature for 72 hours. The reaction mixture was washed twice with one volume of water each, dehydrated over anhydrous sodium sulfate, and concentrated under reduced pressure. The concentrate was crystallized from toluene-hexane (100 ml-100 ml), filtered, and dried in vacuo to give colorless crystals of (RS)-1-p-toluenesulfonyloxy-2-propanol 2a ##STR21## (54 g).

Workup

  1. washThe reaction mixture was washed twice with one volume of water each,
  2. concentrationconcentrated under reduced pressure
  3. customThe concentrate was crystallized from toluene-hexane (100 ml-100 ml)
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-91d5dde2396547c0aa82366412bef1ab
Source dataset
uspto-grants-1988_05
Patent number
US04745066

Reaction notes

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